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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 梁文傑(Man-kit Leung) | |
dc.contributor.author | Chung-Feng Wang | en |
dc.contributor.author | 王鐘鋒 | zh_TW |
dc.date.accessioned | 2021-06-16T10:49:45Z | - |
dc.date.available | 2018-08-16 | |
dc.date.copyright | 2013-08-16 | |
dc.date.issued | 2013 | |
dc.date.submitted | 2013-08-12 | |
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/61154 | - |
dc.description.abstract | 經由正確的分子設計及合理的合成策略,我們開發了新穎的多功能性藍光材料TFDPA及TFDPABT。本論文鉅細靡遺地從分子設計、合成策略與步驟、應用於小分子濕式製程有機發光二極體(organic light-emitting diodes, OLEDs)深藍元件等的優異表現、利用能量轉移製作多色磷光放光元件等應用逐一探討。且由於此系列分子可透過施加電壓誘發聚合反應,我們也一併對電聚合的過程與條件進行探究,並嘗試製作此系列分子電聚薄膜的元件並開發其光電應用。
TFDPA的分子結構包含高螢光性的三聚芴主幹、提供良好溶解度及濕式製程能力的長碳鏈,以及具電洞傳導性質及電聚合能力的三苯胺基團,並具有良好熱穩定性及以濕式製程方式製作電致放光元件的能力。在元件的製作上可以完全省略電洞傳導層(hole-transport layer, HTL)的使用仍維持高效率表現,達成簡化元件製程的目的(simple fabrication)。做為發光材料方面,我們以TFDPA製作效率極高的無摻雜(nondoped)螢光飽和深藍(deep-blue)發光元件,完成了無使用電洞傳導層的濕式製程高效率深藍發光元件,元件放光之CIE座標位於深藍區的(0.17, 0.07),且元件外部量子效率(exerternal quantum efficiency, EQE)高達2.7 %。此外我們也以TFDPA作為主體材料(host material),分別摻雜橘光[Ir(2–phq)3]及紅光[(Mpq)2Ir(acac)]磷光染料,成功地利用能量轉移(energy transfer)的方式,製作出高效率的橘光及紅光磷光放光元件。另更藉由控制適當微量比例黃光磷光材料[(Bt)2Ir(acac)]的摻雜,巧妙利用不完全的能量轉移,以主體材料之深藍光螢光放光,搭配客體之黃光磷光材料放光,以簡易之雙色調控,達成螢光-磷光混成之純白放光元件製作,大舉簡化了一般以多色調控以達成白光元件之複雜製程,且該白光元件放光之CIE座標位於接近純白光區域中心之(0.38, 0.33)。 由於TFDPA的成功,我們在其基礎之上,再加入電子傳導基團,以期達到更多功能性而設計了TFDPABT分子。除了高螢光性的三聚芴主幹外,同時兼納了具電洞傳導性質及電聚合能力的三苯胺基團和具電子傳導性質的PBI(Phenylbenzimidazole)基團。我們以濕式製程方式製作無摻雜的純螢光藍光元件及摻雜磷光染料的紅光元件,發光強度及效率等各項表現均佳。並嘗試用以製作單層結構藍光元件,因高效率可濕式製程的非聚合物OLED單層結構藍光元件至今仍相當少見,這部分研究非常具有潛力,是未來展望的重點。 除了直接以「小分子」的型態應用於有機電致放光元件之外,我們所發明的TFDPA及TFDPABT分子,由於所引入的三苯胺基團具有氧化聚合的特性,透過電化學裝置施加電壓後,將發生聚合反應而形成高分子薄膜於電極之上。經由訂製的電聚合裝置,直接以ITO(indium tin oxide,氧化銦錫)玻璃做為電化學工作電極,並對各項電聚合條件進行最適化後,成功地將高分子發光層沈積於ITO之上,生成有機分子薄膜。另也嘗試將帶有電聚基團的高分子polyvinylcarbazole(PVK)加入進行共電聚合,續以電子顯微鏡及原子力顯微鏡進行不同聚合條件下生成之有機薄膜的鑑定。此外,我們也嘗試直接以電聚合(in situ electropolymerization)發光層後的ITO玻璃進行有機電致放光元件之製做,試圖開發一套以電聚合方式直接製做高分子發光層並應用於電致放光元件的一貫化製程。 除了將電沉積薄膜應用於電致放光元件外,我們另開發其光致放光方面的應用,將圖形化(patterned)後的ITO電極直接以電聚合方式覆蓋上高螢光性的藍光發光材料薄膜,在紫外光源激發下發出高亮度藍光,以提供更多層面的應用。 | zh_TW |
dc.description.abstract | Organic light-emitting diodes (OLEDs) have been recognized as a promising alternative display or lighting technology and have been studied for decades. And because of the intrinsic wide-band-gap nature of deep-blue emitters, it will be a great challenge to develop an efficient and stable blue-emitting material with a Commission Internationale de L’Eclairage (CIE) y coordinate value < 0.10. Although many academic and industrial research endeavors already focused on this topic, saturated deep-blue fluorescent small molecule-based emitters suitable for solution-process to give high efficiency and thermal stability remain relatively rare so far. Solution processability usually requires material with a large molecule size, while the molecular p-conjugation system should not be too extended to ensure the deep-blue emission of the material. In this regard, we designed a new multifunctional blue-emitting terfluorene derivative (TFDPA), which is featured with triphenylamine groups for hole-transportation and long alkyl chains for solution processability on the conjugation inert bridge centers.
TFDPA can give homogeneous thin film by soultion process and exhibits high hole mobility (mh ≈10–3 cm2 V–1s–1) and suitable HOMO for hole injection. Particularly, TFDPA performs efficient deep-blue emission with high quantum yield (~100% in solution, 43% in thin film) and suitable triplet energy (ET = 2.28 eV), making solution-processed OLED devices of using TFDPA as blue emitter and as host for iridium-containing phosphorescent dopants feasible. The solution-processed nondoped blue OLED device gives saturated deep-blue electroluminescence [CIE = (0.17, 0.07)] with EQE of 2.7 %. TFDPA-hosted electrophosphorescent devices performed with EQE of 6.5% for yellow [(Bt)2Ir(acac)], 9.3% of orange [Ir(2–phq)3], and 6.9% of red [(Mpq)2Ir(acac)], respectively. In addition, with careful control on the doping concentration of [(Bt)2Ir(acac)], a solution-processed fluorescece-phosphorecence hybrided two-color–based WOLED with EQE of 3.6% and CIE coordinate of (0.38, 0.33) was successfully achieved. Based on the success of TFDPA, we designed and synthesized another new three-in-one material TFDPABT, which is both a highly luminescent deep-blue emitter and hole-transporting material, and featured with electron-transporting ability. TFDPABT is also a terfluorene derivative and therefore guarantees highly deep-blue luminescence. In addition, it carries triphenylamine groups for hole-transportation and phenylbenzoimidazole groups for electron-transportation. Due to sort of ambipolar property, TFDPABT has suitable HOMO and LUMO for hole and electron injections, which are -5.34 eV and -2.31 eV respectively. We used TFDPABT to fabricate nondoped deep-blue electroluminescence device and it showed efficient emission at saturated deep-blue corner [CIE = (0.18, 0.10)]. TFDPABT-hosted red [(Mpq)2Ir(acac)] electrophosphorescent device also performed well and left no residue luminescence from host, which indicates successful energy transfer. Besides the development of solution-processed, simple fabricated OLEDs which based on monomer TFDPA or TFDPABT, we also tried to study the properties of electrodeposited films. Due to the electropolymeriable triphenylamine moieties carried by TFDPA and TFDPABT, these two emitters could become polymers if electric potential is applied to trigger the polymerization reaction. After some trial-and-error process, we successfully deposited emissive thin films of TFDPA and TFDPABT on electrode through cyclic voltammetry (CV) oxidation and characterized the films by SEM and AFM. Then we used the in-situ electropolymerized thin films directly to fabricate the electroluminescent devices, or deposited the emitters on the patterned ITO glass substrates to develop applications of our novel materials. All the details will be discussed in this dissertation. | en |
dc.description.provenance | Made available in DSpace on 2021-06-16T10:49:45Z (GMT). No. of bitstreams: 1 ntu-102-D95549001-1.pdf: 5872823 bytes, checksum: 712e58d486661c1b964ca54eb70f2a3e (MD5) Previous issue date: 2013 | en |
dc.description.tableofcontents | 目錄
摘要 i Abstract iii 目錄 v 圖目錄 vii 表目錄 xii 第 1 章 緒論 1 1-1 有機電致發光元件之簡介與重要進展 2 1-2 濕式製程高效率深藍電致放光元件之回顧與展望 9 1-3 可電聚合分子之分子設計與發光元件之應用 17 1-4 結論 26 第 2 章 三聚芴衍生物應用於濕式製程之深藍發光元件性質探究 27 2-1 三聚芴分子簡介 27 2-2 具電洞傳導性質之三聚芴TFDPA分子基本性質研究 28 2-2-1 TFDPA分子設計與合成結果 28 2-2-2 TFDPA光物理性質 30 2-2-3 TFDPA熱性質 31 2-2-4 TFDPA電化學性質 33 2-2-5 TFDPA的載子傳輸性質分析 37 2-3 TFDPA應用於濕式製程之電致發光元件性質探究 39 2-3-1 TFDPA做為純螢光深藍發光材料之元件性質探討 39 2-3-2 TFDPA做為主體摻雜磷光發光染料調控多色元件結果探討 44 2-3-3 TFDPA為主體材料之白光元件構想與結果探究 47 2-3-4 TFDPA濕式製程薄膜之形態鑑定 51 2-3-5 TFDPA應用於濕式製程電致發光元件之結果與討論 52 2-4 兼具電洞及電子傳導性質之三聚芴TFDPABT基本性質研究 53 2-4-1 TFDPABT分子設計與合成結果 53 2-4-2 TFDPABT光物理性質 56 2-4-3 TFDPABT熱性質 60 2-4-4 TFDPABT電化學性質 62 2-5 TFDPABT應用於濕式製程之電致發光元件性質探討 65 2-5-1 TFDPABT做為純螢光藍光發光材料之元件性質探討 65 2-5-2 TFDPABT做為主體材料摻雜磷光發光染料元件結果探討 69 2-5-3 TFDPA與TFDPABT混合塗佈之藍光元件性質探究 71 第 3 章 三聚芴衍生物之電聚合現象及應用於光電元件性質之探究 75 3-1 TFDPA與TFDPABT之電聚合現象 75 3-2 TFDPA與TFDPABT電聚合反應條件之調控與結果鑑定 76 3-2-1 電聚合反應裝置改良 76 3-2-2 TFDPA與TFDPABT電聚合薄膜條件探究 78 3-3 電聚合薄膜於電致發光元件之應用與探究 81 3-4 TFDPA與TFDPABT電聚合薄膜鑑定 83 3-5 電聚合薄膜之其他應用 88 第 4 章 結論與展望 91 第 5 章 實驗部份 94 5-1 材料和方法 94 5-2 元件製作與量測 95 5-3 合成步驟與數據 97 參考文獻 104 附錄 1H-NMR與13C-NMR光譜 112 圖目錄 圖1 – 1: Alq3及HTM-2之分子結構……………………………………………………2 圖1 – 2: Coumarin540、DCM1及DCM2之分子結構………………………………….3 圖1 – 3: Holmes等人利用水溶性離子性前趨物製作電致放光高分子PPV之流程圖……………………………………………………………………………...4 圖1 – 4: Platinum-octaethyl-porphyrin (PtOEP)之化學結構…………………...………5 圖1 – 5: 不同陰極金屬對元件效率所造成之影響……………………………………5 圖1 – 6: PEDOT及PSS之化學結構…………………………………………………..6 圖1 – 7: LiF對於電子注入有機層Alq3能階差異的影響…………………………….7 圖1 – 8: Kido等人製作的白光元件結構圖及元件操作情形(該元件結構為ITO/TPD (400A)/p-EtTAZ (30 A) /Alq (50 A)/Nile Red-doped (1 mol %) Alq (50 A)/Alq (400 A)/Mg:Ag)……………………………………………………..8 圖1 – 9: [(Btp)2Ir(acac)]之化學結構……………………………………...………….....8 圖1 – 10: Yang等人發表之星狀分子T1∼T3之化學結構…………………………..10 圖1 – 11: Pei等人發表之螺環三聚茚(spirotruxene)分子衍生物化學結構………11 圖1 – 12: Huang等人發表之六芴(fluorene)取代三聚茚(truxene)分子Tr1~Tr4之化學結構………………………………………………………………….12 圖1 – 13: Ding等人發表具有電洞傳導性質之星狀分子T1∼T4之化學結構……..13 圖1 – 14: Cao等人發表具有電洞傳導性質之星狀分子T1∼T3之化學結構………14 圖1 – 15: Yang等人發表結合anthracene與stilbene之星狀分子化學結構…………15 圖1 – 16: Yang等人發表結合以芴橋接之雙極性分子之化學結構…………………15 圖1 – 17: PbT及NPB之分子結構……………………………………………………19 圖1 – 18: Schroeder等人發表以電聚合PEDOT/PSS對金表面進行改質應用於有機場效電晶體的研究………………………………………………………….19 圖1 – 19: Advincula等人將PVK電聚合於ITO之上當作電洞傳導層使用製作PLED元件………………………………………………………………………….20 圖1 – 20: BT、3-MT及TPD之分子結構……………………………………………21 圖1 – 21: Advincula等人發表之樹枝狀分子G0 ~ G2之化學結構…………………22 圖1–22: Advincula等人發表以特殊前趨物製作電聚合PVK薄膜之方法………...23 圖1 – 23: Ma等人以RGB三色單體進行共電聚合達成白光薄膜概念圖………….24 圖1 – 24: Ma等人以可溶前趨物高分子製作電聚合藍光薄膜概念圖……………...25 圖2 – 1: 芴分子架構與命名 27 圖2 – 2: TFDPA之合成流程圖 29 圖2–3: TFDPA溶液態(1x10-5 M CH2Cl2)及薄膜態之吸收光譜及放光光譜,以及77K下溶液態(1x10-5 M EtOH)測得之磷光放光光譜 31 圖2–4: TFDPA熱重分析圖 32 圖2–5: TFDPA差式掃描熱分析圖 33 圖2–6: TFDPA之氧化還原循環伏特安培法圖 35 圖2–7: TFDPA氧化端之差式脈動伏特安培法圖 36 圖2–8: 飛行時間法(TOF)的量測裝置示意圖 37 圖2–9: TFDPA之光電流和載子傳輸率圖 38 圖2–10: CIE Chromaticity Diagram 色品圖 40 圖2–11: 所選用電子傳導材料TPBI及Bphen之化學結構 41 圖2–12: TFDPA做為無摻雜(non-doped)深藍發光材料(元件B)之電致放光光譜 42 圖2–13: TFDPA做為無摻雜(non-doped)深藍發光材料(元件B)之電致放光表現 43 圖2–14: 深藍發光元件(元件B)各層材料之能階示意圖 43 圖2–15: 多色元件製作所選用之磷光摻雜材料化學結構 45 圖2–16: TFDPA做為主體材料調控多色放光之元件電致放光光譜圖 45 圖2–17: TFDPA做為主體材料調控多色放光之元件表現 46 圖2–18: 白光元件設計概念圖 47 圖2–19: 雙色調控之螢光-磷光混成白光元件(Device W1)電致放光光譜圖 49 圖2–20: 雙色調控之螢光-磷光混成白光元件(Device W1)元件表現 49 圖2–21: (a)無摻雜TFDPA旋轉塗佈製作之薄膜AFM影像 (b)TFDPA摻雜[(Bt)2Ir(acac)] 旋轉塗佈製作之薄膜AFM影像 51 圖2–22: 以TFDPA製作之各有機電致放光元件CIE座標位置圖 52 圖2–23: TFDPABT之合成流程圖 55 圖2–24: TFDPABT於二氯甲烷溶液態及以甲苯溶液旋轉塗佈薄膜態的吸收及螢光放光光譜 56 圖2–25: TFDPABT在不同溶劑系統下之螢光放射光譜 57 圖2–26: TFDPABT在不同溶劑系統下之吸收光譜 57 圖2–27: TFDPABT在不同波長下之螢光激發光譜(右上方小圖為二氯甲烷溶劑中之螢光放射光譜) 58 圖2–28: TFDPABT溶液態的低溫放光光譜 59 圖2–29: TFDPABT熱重分析圖 61 圖2–30: TFDPABT差式掃描熱分析圖 61 圖2–31: TFDPABT之氧化還原循環伏特安培法圖 62 圖2–32: TFDPA與TFDPABT之氧化與還原電位比較圖 64 圖2–33: TFDPA與TFDPABT之能階比較圖 64 圖2–34: 電子傳導材料TAZ之化學結構 66 圖2–35: TFDPABT分子做為無摻雜(non-doped)藍光元件電壓對亮度關係圖. 67 圖2–36: TFDPABT分子做為無摻雜(non-doped)藍光元件外部量子產效率對電流密度關係圖 67 圖2–37: TFDPABT分子做為無摻雜(non-doped)藍光元件電致放光光譜圖 68 圖2–38: TFDPABT分子做為無摻雜(non-doped)藍光元件電致放光座標圖 68 圖2–39: 熱聚合電洞傳導層材料VCL1之化學結構 69 圖2–40: TFDPABT做為主體摻雜紅光磷光染料之元件表現 70 圖2–41: TFDPABT做為主體材料摻雜紅光磷光染料之元件放光CIE座標圖 71 圖2–42: TFDPA與TFDPABT混合塗佈元件於不同操作電壓下之放光情形 73 圖2–43: TFDPA與TFDPABT混合塗佈元件於不同操作電壓下之效率表現 73 圖2–44: TFDPA與TFDPABT混合塗佈元件CIE座標及電致放光光譜 74 圖3–1: TFDPA分子之氧化聚合訊號圖 75 圖3–2: TFDPABT分子之氧化聚合訊號圖 76 圖3–3: 以ITO玻璃做為循環伏特安培法之工作電極使用實況 77 圖3–4: ITO玻璃專用之電聚合裝置使用實況 77 圖3–5: TFDPA分子電聚合薄膜於紫外光激發下之情形 79 圖3–6: TFDPA分子溶液態、旋轉塗佈及電沈積薄膜態之螢光放射光譜比較 80 圖3–7: 元件結構ITO/TFDPA(electrodeposited 25 cycles)/LiF/Al不同電壓下之電流及發光強度關係圖 81 圖3–8: 元件結構ITO/TFDPA(electrodeposited 50 cycles)/LiF/Al不同電壓下之電流及發光強度關係圖 82 圖3–9: 未進行聚合反應之ITO玻璃表面 83 圖3–10: 以TBAP為電解質進行TFDPA氧化循環25圈之電沈積薄膜SEM圖…… .84 圖3–11: 以TBAPF6為電解質進行TFDPA氧化循環25圈之電沈積薄膜SEM圖… 84 圖3–12: TFDPA分子電聚合薄膜於原子力顯微鏡下之觀察 85 圖3–13: PVK化學結構圖 86 圖3–14: 加入PVK與TFDPA所共電沈積之薄膜SEM圖 87 圖3–15: 加入PVK與TFDPA所共電沈積之薄膜經solvent annealing後之SEM圖 87 圖3–16: 將ITO玻璃圖形化示意圖(深色部分代表仍覆蓋ITO部分) 88 圖3–17: 圖形化之ITO玻璃做為電極進行電沈積反應後之薄膜於紫外燈激發下放出藍色螢光。(下方小圖為進行該電沈積實驗時之循環伏特安培法圖) 90 圖3–18: 圖形化ITO電極覆蓋之TFDPA+PVK薄膜SEM圖 90 圖 4–1: TFDPA分子化學結構圖 91 圖 4–2: 以TFDPA製作之各有機電致放光元件操作情形及CIE座標位置圖 92 圖 4–3: TFDPABT分子化學結構圖 92 圖 4–4: TFDPA及TFDPABT的電聚合現象 93 表目錄 表2 – 1: TFDPA各項基本物理性質 35 表2 – 2: TFDPA做為無摻雜(nondoped)飽和深藍發光材料之元件數據 41 表2 – 3: TFDPA做為主體材料調控多色放光之元件表現 45 表2 – 4:雙色調控之螢光-磷光混成白光放光元件(Device W1)表現數據 49 表2 – 5: TFDPA與TFDPABT之各項基本物理性質 63 | |
dc.language.iso | zh-TW | |
dc.title | 功能性三聚芴衍生物應用於濕式製程有機發光材料之開發探究、光電應用及其電聚合性質探討 | zh_TW |
dc.title | Development of Solution-Processable Terfluorene Derivatives and Study of Their Optoelectronic Applications and Electropolymerization Properties | en |
dc.type | Thesis | |
dc.date.schoolyear | 101-2 | |
dc.description.degree | 博士 | |
dc.contributor.coadvisor | 汪根欉(Ken-Tsung Wong) | |
dc.contributor.oralexamcommittee | 洪文誼(Wen-Yi Hung),薛景中(Jing-Jong Shyue),詹益慈(Yi-Tsu Chan) | |
dc.subject.keyword | 深藍螢光,有機發光二極體,濕式製程,白光有機發光二極體,電沈積,電聚合, | zh_TW |
dc.subject.keyword | OLED,deep-blue,non-doped,solution-processable,white light OLED,electrodeposited,electropolymerization, | en |
dc.relation.page | 116 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2013-08-12 | |
dc.contributor.author-college | 工學院 | zh_TW |
dc.contributor.author-dept | 高分子科學與工程學研究所 | zh_TW |
顯示於系所單位: | 高分子科學與工程學研究所 |
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ntu-102-1.pdf 目前未授權公開取用 | 5.74 MB | Adobe PDF |
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